(3R,6R)-6-(tert-butyldimethylsilyloxy)hept-1-en-3-ol | 1206196-00-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,6R)-6-(tert-butyldimethylsilyloxy)hept-1-en-3-ol
• 英文别名: (3R,6R)-6-[tert-butyl(dimethyl)silyl]oxyhept-1-en-3-ol
• CAS: 1206196-00-0
• 化学式: C₁₃H₂₈O₂Si
• 分子量: 244.45
• InChiKey: FIAMANTWQDHSNF-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,6R)-6-(tert-butyldimethylsilyloxy)hept-1-en-3-ol 、 溴甲苯 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以78%的产率得到((2R,5R)-5-(benzyloxy)hept-6-en-2-yloxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Studies directed toward the first total synthesis of acremodiol and acremonol

  摘要：

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.030
• 作为产物：
  描述：

  在 sodium 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以73%的产率得到(3R,6R)-6-(tert-butyldimethylsilyloxy)hept-1-en-3-ol
  参考文献：
  名称：

  Studies directed toward the first total synthesis of acremodiol and acremonol

  摘要：

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.030

文献信息

• Stereoselective total synthesis of stagonolide E
  作者：Gowravaram Sabitha、P. Padmaja、P. Narayana Reddy、Surender Singh Jadav、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.09.072

  日期：2010.11

  The first total synthesis of a 10-membered macrolide, stagonolide E is described from readily available 4-penten-1-ol. The synthetic strategy involves Jacobsen’s kinetic resolution, Sharpless epoxidation, Stille–Gennari, and Yamaguchi lactonization as key reactions.

  从容易获得的4-戊烯-1-醇中描述了10元大环内酯类的第一个全合成内酯。合成策略涉及Jacobson的动力学拆分，Sharpless环氧化，Stille–Gennari和Yamaguchi内酯化等关键反应。
• Stereoselective Total Synthesis of (-)-(6R,11R,14R)-Colletallol via RCM Protocol
  作者：Palakodety Krishna、D. Ramana、B. Reddy

  DOI：10.1055/s-0029-1218270

  日期：2009.11

  The total synthesis of (-)-colletallol via a ring-closing metathesis protocol is reported. (-)-colletallol - ring-closing metathesis (RCM) - Grubbs II catalyst - Jacobsen’s hydrolytic kinetic resolution (HKR)

  报告了通过闭环复分解方案的（-）-Colletallol的总合成。 （-）-Colletallol-闭环复分解（RCM）-Grubbs II催化剂-Jacobsen的水解动力学拆分（HKR）
• Studies directed toward the first total synthesis of acremodiol and acremonol
  作者：Gangavaram V.M. Sharma、Samala Mallesham、Chirutha Chandra Mouli

  DOI：10.1016/j.tetasy.2009.10.030

  日期：2009.11

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.